Madonna is a visual artist who’s cinematic in her approach to pop music. That said, her relationship with cinema has been diffident, at best. Despite an exciting film debut in Susan Seidelman’s 1985 comedy, Desperately Seeking Susan, Madonna’s film career has been bogged down by a string of terrible flops in which she flailed. Even if she was a magnetic presence in her music videos, her film career betrayed an inability to transfer that charisma to a full-length film.
The movie moments in which she did shine usually derived from her essentially playing a version of herself (Madonna: Truth or Dare). Outside of that, it’s when she was a supporting player, leaning on her natural sense of comedy (A League of Their Own). When burdened with being a lead actor, though, the superstar hits a wall. The most successful part of Madonna’s relationship with Hollywood is, of course, her music.
While she was determined to prove herself as an actress, the few bright spots in her film forays were due to her music. James Foley’s 1987 strained screwball comedy— Who’s That Girl?—failed to turn Madonna into a 1980s Carole Lombard, but she did enjoy a number one hit record with the film’s theme tune. Even if she was little more than window dressing (channeling Veronica Lake in Warren Beatty’s Dick Tracy vanity project), she stretched her musical muscles and creativity. How? By folding in torch songs, novelty numbers, and Broadway showstoppers on the accompanying album.
Indeed, the Dick Tracy soundtrack is an essential moment in the pop star’s career because it predicted her sole (qualified) film triumph, 1996’s Evita. Unfortunately, the long-awaited film version of the Andrew Lloyd Webber 1978 musical was in production hell for years. A significant reason for why is that there were a variety of actresses attached, including Meryl Streep, Liza Minnelli, Sarah Brightman, Barbra Streisand, and Michelle Pfeiffer. (One can source Pfeiffer’s hesitant, if capable, rendition of “I’d Be Surprisingly Good for You” from the musical on the Internet.)
In retrospect, casting Madonna as the controversial Argentine first lady, Eva Perón, feels like a no-brainer. Like Madonna, Perón was a single-mindedly ambitious woman who sought fame, fortune, and power. Crucially, however, Perón’s reality is far darker and more complex. Fortunately, the musical (and its hit tune, “Don’t Cry for Me, Argentina”) does a great job of obscuring the despotic aspect of Perón’s life and career. Madonna herself participated in the scrubbing of Perón’s legacy while peddling the movie in press junkets. After all, drawing parallels between the two iconic women was just too tempting to pass up. Madonna herself invoked the rags-to-riches narrative when finding some shared qualities between herself and Perón, saying:
[I identified with] the arc of her life… the way she, as a teenager, left this very small town that she came from, in the middle of nowhere and just bravely put herself on a train and took herself to the big city without knowing anyone and without having any formal education, or training…. I can relate to that. I came from a small town, and I moved to New York when I was 17…. I think we both needed to have a certain amount of fearlessness to do what we did.
People were immediately skeptical at the prospect of Madonna being the lead in Alan Parker’s film. The biggest concern was whether she could handle the score. For years, critics underestimated her singing voice, and they doubted her ability to sing musical theater. Of course, it didn’t help that vocal powerhouse Patti LuPone created the role on Broadway. Yet, a thorough review of Andrew Lloyd Webber’s work (alongside lyricist Tim Rice) makes the misgivings seem silly. Let’s be frank: Andrew Lloyd Webber is hardly Georges Bizet. Lloyd Webber’s best work is based in pop music, something at which Madonna excels. Also, by the mid-’90s, Madonna had grown and developed as a lyricist and pop composer, and her greatest work was stronger than much of Lloyd Webber’s compositions. So, any questions regarding her being up for the challenge were wholly unwarranted.
Though her film career was defined by mediocrity, by 1996, Madonna had amassed a legendary pop legacy. She’d entered the decade as a stateswoman of popular music, one of the few titans of ’80s MTV pop who was able to maintain her superstardom. However, as a provocateur, she was beginning to suffer from severe backlash. Steeped in misogyny and ginned up by the Culture Wars of the early 1990s, Madonna’s very public persona began to overwhelm her music career. Her 1992 album, Erotica, was released alongside a coffee table book, Sex, and moral purists assailed both projects. (Specifically, they suggested that Madonna was responsible for the moral decline of American culture.) Her eventual shuffle towards middle-class respectability with a project like Evita seemed inevitable and (like everything else in her career) calculated.
From the raw carnal work of Erotica, Madonna released an album of soft R&B, Bedtime Stories, in 1994. Then, in 1995, she put out her third greatest hits compilation, Something to Remember, a collection of her biggest ballad hits. Its liner notes hinted at, if not regret, certainly exhaustion at being a constant source of infamy:
So much controversy has swirled around my career this past decade that very little attention ever gets paid to my music…. While I have no regrets regarding the choices I’ve made artistically, I’ve learned to appreciate the idea of doing things in a simpler way.
In a career defined by a series of musical makeovers, Madonna’s work in Evita equally represented her most extreme and conservative musical guise. Working with vocal coach Joan Lader, she found hidden strengths in her voice. While an engaging and thoroughly enjoyable singer, Madonna will never be considered a world-class technical vocalist. Part of Madonna’s initial charm was her DIY punk spunk. On her classic early tunes, like “Holiday” and “Lucky Star”, her hiccupping trill is fun and funky, making her a relatable pop goddess. (One of the things about Madonna’s initial appeal was that she felt very democratic as a superstar. In other words, her stardom made it seem like anyone could be a pop star if they worked hard enough.) Under Lader’s tutelage, however, she found “parts of [her] voice that [she] never thought [she] had.”
With her newly expanded vocal range, Madonna took on the seemingly daunting task of recording an album’s worth of Broadway show tunes. Because she was working on a film version of the musical, she had a couple of obvious advantages over, say, LuPone or West End vet Elaine Paige. For one thing, she wasn’t performing the material live on stage several times a week. Plus, the recording studio offered her the safety of not having to project to the cheap seats. Lastly, the fragility and delicacy of Madonna’s singing voice allowed her to convey vulnerability in ways that the leather-lunged LuPone or Paige simply couldn’t.
A thorough listen to the soundtrack to Evita shows Madonna at her then-vocal peak. Though her range is still quite limited, she can offer various colors and shades in her singing. She expertly conveys haughtiness and attitude (something she’d been doing in her music for years), and she’s also able to pierce listeners’ hearts. So much of Madonna’s music is glittery and sparkly that it’s easy to underrate her more sincere moments.